反応 #40468

反応方程式

4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester

Intermediate 17

4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester

tributyltin hydride

AIBN

→

4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester

収率 85.0%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度to cool down
2. 2
   濃縮was concentrated to dryness
3. 3
   その他The residue was partitioned into 15% 1M HCl in acetonitrile and hexane
4. 4
   抽出The separated hexane phase was extracted two times with the acetonitrile solution
5. 5
   洗浄The combined acetonitrile solutions were washed with hexane two times
6. 6
   濃縮concentrated
7. 7
   その他The residue was partitioned into ether and 1M K2CO3
8. 8
   洗浄The separated ether phase was washed successively with 0.4M Na2S2O3 and brine
9. 9
   乾燥dried over MgSO4
10. 10
    濃縮concentrated
11. 11
    その他The residue was purified on silica (7.5% EtOAc/hexane)

実験手順

To a solution of 4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester (Intermediate 17, 1.23 g) and tributyltin hydride (1.8 ml, 2.5 eq.) in 11 ml of toluene under gentle reflux was added over 1.5 hr a solution of AIBN in toluene (25 mg/1 ml). The mixture was allowed to cool down and was concentrated to dryness. The residue was partitioned into 15% 1M HCl in acetonitrile and hexane. The separated hexane phase was extracted two times with the acetonitrile solution. The combined acetonitrile solutions were washed with hexane two times and concentrated. The residue was partitioned into ether and 1M K2CO3. The separated ether phase was washed successively with 0.4M Na2S2O3 and brine, dried over MgSO4 and concentrated. The residue was purified on silica (7.5% EtOAc/hexane) to give 760 mg (oil, 85% yield) of compound 4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester.

出典